Rigid macrocyclic triamides as anion receptors: Anion-dependent binding stoichiometries and 1H chemical shift changes

Kihang Choi, Andrew D. Hamilton

Research output: Contribution to journalArticle

127 Citations (Scopus)

Abstract

The cyclic triamide of 3′-amino-3-biphenylcarboxlic acid is readily synthesized in a stepwise manner and represents a novel class of anion receptors with a large central cavity. This macrocycle binds more strongly to tetrahedral anions than spherical or planar anions in organic solvents. The binding stoichiometries for anions with symmetrical charge distribution depend on the solvent polarity, while tetrahedral p-tosylate binds to the macrocycle with 1:1 stoichiometry in all solvents studied. The 1H NMR chemical shift changes of the protons lining the interior of the macrocycle's central cavity also depend on the geometry of the bound anion. The importance of the convergent array of hydrogen bond donors for anion binding by the macrocycle was confirmed by control studies with an acyclic triamide and a macrocycle with intramolecular hydrogen bonds.

Original languageEnglish
Pages (from-to)10241-10249
Number of pages9
JournalJournal of the American Chemical Society
Volume125
Issue number34
DOIs
Publication statusPublished - 2003 Aug 27

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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